Oregano
by elwarre
Summary: "Green eyes, buzzing—weed alone doesn't conjure up that kind of scenario. Isn't that right, Sam?" "Dude, I was eighteen." (Episode tag for 11x19; Sam/Jess/Brady, Sam/Dean; Jess POV)
_Warnings/kinks: recreational drug use, d/s overtones, threesome, pegging_

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Sam's a little wary of the bowl, glares at it with that tiny wrinkle between his eyebrows like he's daring it to bite him. They're sharing the couch in Jess's dormroom, loose and easy after a couple of beers and a healthy serving of Cuervo, and Brady's smirking languidly at them from his perch in her armchair. He's already high, Jess thinks.

She's known Brady forever, but she's only been friends with Sam for a handful of months. In took less than half that time for her to swear upon all the heavenly hosts to a) get Sam to relax, and b) fuck him. Preferably both at the same time.

For most of first semester Sam was just Brady's mysterious roommate who kept ugly plants on his windowsill and boxes of newspaper clippings in his desk, who carved strange patterns into his bedposts. She hardly ever saw him.

Then Thanksgiving rolled around. Brady's dad was on some business trip in Malaysia, so Brady stayed in town, and Jess stayed to keep him company. The night before the big day itself they walked into Brady's room to find Sam shredding what appeared to be a carefully handwritten letter in the trashcan. He was shaking.

They didn't ask—Jess, because she _could_ be sensitive when she wanted to be, Mother, and Brady likely because he didn't care. But they did invite Sam to join what Jess was gleefully calling their Save the Turkey Day celebrations. They bundled up in parkas and sat on the beach eating tofurkey sandwiches and talking about their classes but not their families.

See? Sensitivity.

Anyway, at one point Sam launched into an impassioned tirade against their lit prof's hero-worship of "Hemingway's incessant misogynistic douchebaggery" that had Jess breathless with laughter and maybe, possibly, just the tiniest bit in love.

After that, they were friends. She'd decided. He never stood a chance against her.

But Sam, for all that he smiled and listened and seemed genuinely attentive to her admittedly non-interesting rants about neoclassical art, remained a closed book. Questions about his family got her nowhere. Questions about his past got her nowhere. A request to change a flickering lightbulb in her room that she couldn't quite reach _did_ get her a response, though not one she understood. The temperature in her bedroom was just fine, thank you very much, and the only strange noises she heard at night were her irritatingly horny neighbors.

So she plotted.

All it took, in the end, was a half-drunken late-night study session. Sometime after three in the morning she closed her textbook and told him point-blank that she'd seen the way he looked at her, and she'd seen the way he looked at Brady, and that for the love of all that was holy, he needed to relax. She had a plan, she said, and he agreed to it.

But now he's hunched over on her couch, glancing between her and the bowl and Brady, anxious and restless and desperate to just let go.

So she laughs and pokes him with her toe, says, "You wanted to be high for this, remember?" and Sam smiles at her, all bewildered gratitude and eager-to-please, and he flicks the lighter and breathes in the smoke. His nostrils flare when he coughs, and soon enough he's laughing, too, loud, bright laughter with his cheeks flushed red and his head thrown back, and she can't help it, she _can't_ , just climbs right into his lap and puts her tongue on his neck.

She feels him startle, feels him start to stiffen in his pants, and Brady must take the bowl from him then because suddenly those big, broad hands are climbing up her back, under her shirt, tracing the ridges of her spine and the soft sides of her breasts. She grinds down a little and bites his neck, right there where it meets his shoulder, meaty and thick in her teeth. There's a strangled sort of sound in his throat, and she does it again.

She takes another hit when Brady offers, and Sam's watching her with hungry eyes and his mouth hanging open, so wet and so pink, and she presses her lips to his and breathes out, slowly, and this time Sam sucks it in like he's dying for it.

Brady puts the bowl somewhere, who cares, comes back and tugs the hem of her shirt up over her head and she stretches with it, watches her breasts bounce as she moves. Sam watches, too, squeezing her waist and biting at his lip while Brady reaches around to palm her. She grins and shoves Sam down on the couch, slides up his body and plants herself right on his face.

Her panties are damp already, she's aching and hot and she wants his tongue and he gives it to her. Whatever uncertainty he felt before seems to be gone. His fingers grip bruises into her hips and he thrusts his tongue hard, once, twice, then he growls a little and sucks her panties into his mouth, sucks the taste of her right out of them and his eyes roll back in his head and he groans.

She hears his zipper being undone, knows what Brady's getting up to back there but she can't see, Brady knows she can't see, and that's just monumentally unfair. She climbs off Sam, ignores his whine and steps out of her panties. They're soaked anyway, useless, so she tosses them to the floor and straddles Sam again, facing Brady this time, and Sam's tongue comes back and _oh_ , that's better.

It's all slickness and heat and her vision blurs, doubles, eyes falling closed, opening to see Brady slide Sam's pants down and she figured he'd be big, but _seriously_. Brady's eyeing him with a lazy shark's grin as he slicks up his fingers and times it just right so he swallows him down while his finger slides in, and Sam jerks so hard he knocks Jess to the floor.

Sam babbles apologies, but Brady won't stop sucking and Jess won't stop laughing so he relents and lies back down. Brady pushes one of Sam's thighs right up to his chest and that's a view, _yes_ , Sam spread and helpless with a mouth on his dick and a finger in his ass, so she settles in and reaches between her legs to rub herself.

He's shaking now, close, and she pinches her clit and thinks about all the ways she'd like to have him. She could tie him naked to his little twin bed, bite his nipples and suck his balls 'til he's hard and frantic, make him whine and beg so pretty before she finally slides onto his dick and rides him. Or maybe in the library, she could hide him in the bathroom while she locks up after her shift, pull him into a study room and down over her lap and turn his ass bright red. Tell him to be still, be a good boy, take what she gives him.

She could take him home to meet her parents and fuck him in their dining room.

She's getting ahead of herself, she knows, second semester freshman year and she hasn't even fucked him yet, for Christ's sake, but he's smart and a smartass and he's all big dimples and big hands and those big, broad shoulders that just beg for someone to take care of him, _please_ , and—

God, she knows what he needs.

She stands up, a little shaky, puts her fingers in her mouth and sucks them clean. Sam's watching her, panting. She winks at him as she walks away.

She knows right where it is, hidden beneath a pile of bras in the top drawer of her dresser, and she's never been more grateful that her parents shelled out for a private room. She tucks it to her chest and heads for the bathroom, angled away from Sam so he can't see what she's doing. His surprise will be delicious.

She fiddles with the straps in the mirror. Considers removing her little black skirt, decides against it. She likes the way the fabric bulges over the red silicone. She studies her face, scrubs at the mascara smeared under her eyes, and adds a little lipstick to match the dildo.

Brady's still going at it when she comes back, three fingers deep and sucking away while Sam writhes and whimpers on the couch. "Brady," she says, and he knows that voice, they've played before, and he stops, sits back, wipes his clean hand over his mouth and looks at her.

Sam whines, looks over with a half-formed pout and freezes when he sees her. Then he's beet red, mouth gaping like a fish and she wants _so badly_ to laugh but she won't. She keeps her gaze indifferent as she studies him.

"Brady," she says again, "go get on the bed, back propped up against the pillows. No clothes."

It's not so much Brady's thing, that kind of submission, but they've switched around a few times just for the fun of it, and he'll go along with her tonight. He strips off his clothes, bare chest gleaming in the lamplight. It's a small room, just a bed and a couch and a chair, really, but Brady takes _forever_ to walk across it. She makes herself wait, though, wait until he's situated on the bed, legs spread like she wants them, before she looks back at Sam.

Sam looks debauched. His shirt is soaked in her slick and his spit, his cock is bobbing, angry and red, and he's still got one leg hiked up to his chest. He's trembling, waiting for her command, and good lord if that boy doesn't know what he needs than someone's got to show him.

"Take off your shirt," she says, and he shoots up to obey, eyes never leaving her face. His hands flutter when he's done, like he doesn't know what to do with them, but he doesn't even try to touch his dick. _Good boy_ , she thinks, but doesn't say it. Not yet.

"You're going to thank Brady for being so nice to you," she says. "Now," she adds, when he hesitates.

He stumbles over to the bed, a little bow-legged, and climbs over Brady. He wraps his fingers around Brady's dick and looks at it. He seems hesitant, shy, maybe, which is interesting. She meets Brady's eyes over Sam's head and Brady smirks.

Jess kneels behind Sam and strokes his hip, reaches around to take his hand. Sam twists around and blinks at her owlishly. She smiles. "You ever sucked a dick before?"

Sam sputters, mouth falling open, and that's all the confirmation she needs. "That's ok, sweetie," she says. "Do you want to?" Sam nods, quickly, eyes darting around like he can't bear to look at her, so she pulls him in for a kiss.

He's pliant in her hands, still breathing hard but relaxing now with his mouth on a woman, doing something he knows. She leans back a bit, holds his face so he can't look away. "You'll do great," she says, smiling again. "Just think about what you like, ok?"

Sam takes a breath and she feels the moment he decides to give in, to take what he needs, to let her give it to him. He turns away, rests his hands on Brady's hips and sucks him down.

Sam's an all-in kind of guy, she thinks, watching the hard planes of his back shift while he works. The sort of guy who'll stick around, who'll set his mind to something and go for it. She respects that in a person. She's gotten shit all her life for being stubborn, but stubborn, she knows, is just another word for determined, and determination's what's kept her alive.

She brushes her fingers over Sam's back, around his narrow waist, down the curve of his hip. He shivers under her hands, arches a little when she reaches his ass. "Sam," she says, because it has to be obvious what she plans to do, but she needs to ask anyway. He pulls off Brady with a slurp and looks up through his eyelashes.

God almighty. "Can you tell me what you want?" she asks, and he melts, flushes even brighter, bites his lip and stares at her strap-on longingly like he hopes that'll be enough. She lifts his chin with her finger, makes him meet her eyes. "I need you to say it for me."

"Can you," Sam mutters, "I want you to. Fuck me. Please."

"You want me to fuck you while you blow Brady?" Needs to be sure.

His breath leaves him in a whoosh. "Yes. God, yes. Please."

She smiles. "Such a good boy," she says, stroking his cheek. His eyes flutter shut with the praise.

Sam gets back to work, more confident now. She palms at his ass and he spreads his legs wider. "Oh honey," she says. "You're desperate for it, aren't you."

Sam chokes, squirms a little, but he doesn't stop sucking and he doesn't try to hide, so she takes that for a yes. She gets up to find the lube, slicks her fingers up with it, and kneels back behind Sam. He should still be plenty open—Brady did a thorough job—but she's pretty sure this is a first for him, and anyway, she wants to toy with him a little.

Her finger slides in, smooth and easy. Sam groans around Brady's dick. "No one's ever done this for you, have they? Such a sweet boy, and no one to give you what you need." She adds a second finger beside the first, rubs at his prostate. He jerks, and she runs her other hand down his thigh to soothe him. "Don't worry, honey. I'll take care of you."

She fucks him like that for awhile, slow drag of fingers in and out of his ass, twisting and prodding until he's shoving himself against her for more. She pulls her fingers out and rubs at him with the dildo. "I bet you've tried it yourself, though, haven't you. Jerked off on your bed with your legs spread wide and a finger up your ass, maybe kept a toy hidden where no one can find it, for when you get really desperate. Your own dirty little secret, that toy, and how badly you need it." She slides in, just the tip, and Sam keens. He tries to push back, take her deeper, but she grabs his hips and holds him steady. He bows his back and lets her.

She slides out, works in again, a bit more this time, and Sam's trembling, working slavishly at Brady's dick, but Brady's staring off into space, and she knows how long it takes him to come when he's high. She palms at Sam's ass, pulls it open. Watches, fascinated, as she slides the whole way in, his skin stretched wide around red silicone. There's a groan from Sam, long and drawn-out, helpless.

"That's it, baby," she croons. "Just relax." She's flush with him now, thighs pressed together. He's warm, sturdy, and she rubs at his thighs, reaches around to grab his dick.

"J-Jess," he stammers, pushes into her hand and then back against the dildo. The angle is awkward, but she manages enough leverage to thrust while he fucks up into her hand. His ass clenches around her, bunch and release of solid muscle, mirrored in the lines of his back and the straining tendons of his arms as he struggles to keep himself together, struggles and fails, and comes all over her sheets.

She fucks him through it, keeps on thrusting and groping until he's loose and compliant, and she falls on the bed next to him. He's forgotten Brady in his haze, too much pot and too much sex and too many weeks of not enough sleep and he curls up against her, trembling faintly and sated.

Jess watches them awhile. Sam's warm against her, his shallow breaths tickling her shoulder, and Brady's stroking his dick with the lazy indifference he's always had toward sex, especially when he's high. It's not as big as Sam's, but it's a nice dick and she's still horny so she pulls him over to the couch, wraps him up in a condom, and rides him.

It's later, after she and Brady have fallen asleep in a sweaty tangle on her hand-me-down couch, that she hears Sam's phone ring. He answers with a muffled hello, tells whoever it is on the other end that he's high and he just got fucked in the ass and then, very clearly, "wish it was you, Dean."

She wonders about that, off and on, over the next year or so. Wonders who Dean is, why he turned Sam down. How anyone could see what she sees, have what she has, and reject it. She forgets, eventually, and when she finds a picture of two little boys in Sam's nightstand and he says the name, she fails to make the connection. It's not until he comes to take Sam away, all cocky and bright-eyed in the shadows of their house, that she sees Sam's face when he says Dean's name and remembers.


End file.
